The availability of skilled professionals is a challenge in many rural areas. At the same time, rural youth often view their prospects as limited and pursue higher education less frequently than urban youth. Students’ future study and career choices are influenced by social or cultural background, geographic location, and community resources. Consequently, rural schools may face the challenge of providing opportunities for students to develop skills that enable them to contribute to their personal growth as well as the development of their community. This project, involving three rural municipalities and three elementary schools, focuses on the possibilities for rural schools to promote entrepreneurship in a digitized world. Here, entrepreneurship is based on the idea of relationships and mutual concerns as starting points for developing and acting on opportunities in diverse contexts. Analyses of documents, field notes, and interviews reveal that municipal officials, principals, and teachers, are interested in using digital tools in education to enhance the connections between school, working life, and the surrounding community, which are limited by long distances. For instance, digital field trips to private and municipal enterprises and institutions have been tested as a method. The goal is to provide future-oriented education that highlights opportunities for digital location-independent occupations while also strengthening students’ sense of connection to their local community. However, promoting entrepreneurship by fostering students’ development of creativity and innovation remains a challenge for some schools.